GB1072118A - Amides of aminopropionic acid - Google Patents
Amides of aminopropionic acidInfo
- Publication number
- GB1072118A GB1072118A GB4679863A GB4679863A GB1072118A GB 1072118 A GB1072118 A GB 1072118A GB 4679863 A GB4679863 A GB 4679863A GB 4679863 A GB4679863 A GB 4679863A GB 1072118 A GB1072118 A GB 1072118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amide
- stearylamine
- acid
- methylation
- amidation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title abstract 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 title 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 10
- 230000011987 methylation Effects 0.000 abstract 10
- 238000007069 methylation reaction Methods 0.000 abstract 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 10
- 230000009435 amidation Effects 0.000 abstract 9
- 238000007112 amidation reaction Methods 0.000 abstract 9
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 abstract 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- UQTBADOQMIRHSO-UHFFFAOYSA-N 2-(octadecylamino)propanoic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(C)C(O)=O UQTBADOQMIRHSO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 4
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 4
- 238000005956 quaternization reaction Methods 0.000 abstract 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 3
- 150000005690 diesters Chemical class 0.000 abstract 3
- 238000004043 dyeing Methods 0.000 abstract 3
- 235000003891 ferrous sulphate Nutrition 0.000 abstract 3
- 239000011790 ferrous sulphate Substances 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- JQKCVPDJFGBSRM-UHFFFAOYSA-N octadecan-1-amine;propanoic acid Chemical compound CCC(O)=O.CCCCCCCCCCCCCCCCCCN JQKCVPDJFGBSRM-UHFFFAOYSA-N 0.000 abstract 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- 230000021736 acetylation Effects 0.000 abstract 2
- 238000006640 acetylation reaction Methods 0.000 abstract 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229940106681 chloroacetic acid Drugs 0.000 abstract 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 238000007046 ethoxylation reaction Methods 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- MBHYAZZTHWGCDX-UHFFFAOYSA-N 2-(octadecylamino)propanamide Chemical compound C(CCCCCCCCCCCCCCCCC)NC(C(=O)N)C MBHYAZZTHWGCDX-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- WZBLTGUUMZTWGP-UHFFFAOYSA-N C(CC)(=O)O.C(CC)(=O)O.C(CCCCCCCCCCCCCCCCC)N Chemical compound C(CC)(=O)O.C(CC)(=O)O.C(CCCCCCCCCCCCCCCCC)N WZBLTGUUMZTWGP-UHFFFAOYSA-N 0.000 abstract 1
- KDMNODCAXWDBHM-UHFFFAOYSA-N CN(CCC)C.C(CCCCCCCCCCCCCCCCC)NC(C(=O)O)C Chemical compound CN(CCC)C.C(CCCCCCCCCCCCCCCCC)NC(C(=O)O)C KDMNODCAXWDBHM-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 239000001164 aluminium sulphate Substances 0.000 abstract 1
- 235000011128 aluminium sulphate Nutrition 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 238000005282 brightening Methods 0.000 abstract 1
- 238000007623 carbamidomethylation reaction Methods 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000434 metal complex dye Substances 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000006289 propionylation Effects 0.000 abstract 1
- 238000010515 propionylation reaction Methods 0.000 abstract 1
- 238000004513 sizing Methods 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Novel basic amides are prepared by first reacting 1 to 2 mol of an ester of acrylic acid with a volatile alcohol, at a temperature below 100 DEG C. at which no substantial amidation occurs, with one mol. of primary, secondary or tertiary amine of the formula <FORM:1072118/C2/1> to form an ester-amine which is then further heated with 1 to 2 mol. of a primary, secondary or tertiary amine of the formula <FORM:1072118/C2/2> to form an amide-amine with simultaneous splitting off of an alcohol, said amide-amine being subsequently alkylated, alkoxylated and/or quaternated and/or acylated if desired, one of R1, R2 and R3 representing C12- 24 alkyl or alkenyl, each of the remaining five of R1 to R6 representing hydrogen or C1- 6 alkyl or hydroxyalkyl, A1 and A2 each representing a C2- 6 alkylene radical and each of m and n representing 0 or an integer of from 1 to 6 inclusive provided that at least one represents an integer. Examples describe the preparation of (1) a 1 :2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,6-hexamethylene-diamine and either ethoxylation and quaternization, methylation, or propionylation and methylation of the resulting stearylamino-dipropionic acid di-1-aminohexyl-6-amide; (2) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,3-propylenediamine and either ethoxylation and quaternization, methylation or acetylation and methylation of the resulting stearylamino-propionic acid 1-aminopropyl-3-amide; (3) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,2-ethylenediamine and either methylation or methylation and acetylation of the resulting stearylamino-propionic acid 1-aminoethyl-2-amide; (4) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1,6-hexamethylenediamine and either methylation, alkoxylation or alkoxylation and quaternization (with monochloracetic acid) of the resulting stearylamino-propionic acid 1-aminohexyl-6-amide; (5) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1-amino-3-dimethylaminopropane and either methylation or carbamidomethylation (with chloroacetamide) of the resulting stearylaminopropionic acid 1-dimethylaminopropane 3-amide; (6) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of diethylene-triamine and methylation of the resulting monostearylamino-propionic acid amide of diethylene-triamine; (7) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,3-propylene-diamine and methylation of the resulting stearylamino-dipropionic acid di-1-aminopropane-3-amide; and (8) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1-amino-3-dimethylaminopropane and quaternization of the resulting stearylamino-dipropionic acid di-3-dimethylamino-propane-1- amide with either methyl sulphate or chloroacetamide.ALSO:Novel amino-amides containing a C1- 24 alkyl or alkenyl group in addition to C1- 6 alkyl or hydroxyalkyl groups (see Division C2) are alkoxylated and, if desired, further quaternated or acylated. The amino-amides and their quaternary derivatives may be used as polymerization emulsifiers. In examples a stearylamine - dipropionic acid di - 1 - aminohexyl-6-amide is ethoxylated with up to 75 mols. of ethylene oxide and subsequently quaternized with dimethyl sulphate and alternatively with chloroacetic acid; a stearylamine-propionic acid 1-aminopropyl-3-amide is ethoxylated with up to 30 mols. of ethylene oxide and subsequently quaternized with monochloroacetic acid or alternatively dimethyl sulphate, benzyl chloride, chloroacetamide, glycolchlorohydrin or epichlorohydrin; a stearylaminopropionic acid 1-aminohexyl-6-amide is propoxylated with 2.4 mols. of propylene oxide and subsequently quaternized with chloroacetic acid; a stearylamine-propionic acid 1-aminohexyl-6-amide quaternized with 2 mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, vinyl acetate, ferrous sulphate and hydrogen peroxide; and a stearylamine-propionic acid 1-aminopropyl-3-amide methylated with two mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, ethyl acrylate, butyl acrylate, acrylonitrile, ferrous sulphate and hydrogen peroxide; the polymer emulsions may be used for treating textiles or paper.ALSO:Novel amino-amides containing a C12-24 alkyl or alkenyl group in addition to C1-6 alkyl or hydroxyalkyl groups (see Division C2) and their quarternary or alkoxylated derivatives are used as levelling agents in dyeing baths or as emulsifying agents in emulsion polymerization systems, to which they impart improved paper sizing properties. In examples the products are used in a dyebath containing 2:1 metal complex dyes, ammonium sulphate, and formic acid to obtain a level dyeing effect on striped dyeing nylon woven material, and in an emulsion polymerization system containing aqueous sodium bisulphite, ferrous sulphate, hydrogen peroxide, ethylacrylate, butyl acrylate and acrylonitrile, this being used to size bleached sulphite cellulose in conjunction with rosin size, aluminium sulphate, kaolin and an optical brightening agent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1414962 | 1962-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1072118A true GB1072118A (en) | 1967-06-14 |
Family
ID=4398397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4679863A Expired GB1072118A (en) | 1962-12-01 | 1963-11-27 | Amides of aminopropionic acid |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT258875B (en) |
| BE (1) | BE640639A (en) |
| GB (1) | GB1072118A (en) |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664848A (en) | 1982-12-23 | 1987-05-12 | The Procter & Gamble Company | Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties |
| US8969353B2 (en) | 2008-11-07 | 2015-03-03 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US9006487B2 (en) | 2005-06-15 | 2015-04-14 | Massachusetts Institute Of Technology | Amine-containing lipids and uses thereof |
| US9181321B2 (en) | 2013-03-14 | 2015-11-10 | Shire Human Genetic Therapies, Inc. | CFTR mRNA compositions and related methods and uses |
| US9193827B2 (en) | 2010-08-26 | 2015-11-24 | Massachusetts Institute Of Technology | Poly(beta-amino alcohols), their preparation, and uses thereof |
| US9227917B2 (en) | 2012-08-13 | 2016-01-05 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US9308281B2 (en) | 2011-06-08 | 2016-04-12 | Shire Human Genetic Therapies, Inc. | MRNA therapy for Fabry disease |
| US9315472B2 (en) | 2013-05-01 | 2016-04-19 | Massachusetts Institute Of Technology | 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof |
| US9522176B2 (en) | 2013-10-22 | 2016-12-20 | Shire Human Genetic Therapies, Inc. | MRNA therapy for phenylketonuria |
| US9629804B2 (en) | 2013-10-22 | 2017-04-25 | Shire Human Genetic Therapies, Inc. | Lipid formulations for delivery of messenger RNA |
| US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
| US9850269B2 (en) | 2014-04-25 | 2017-12-26 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US9957499B2 (en) | 2013-03-14 | 2018-05-01 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US10022455B2 (en) | 2014-05-30 | 2018-07-17 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10138213B2 (en) | 2014-06-24 | 2018-11-27 | Translate Bio, Inc. | Stereochemically enriched compositions for delivery of nucleic acids |
| US10576166B2 (en) | 2009-12-01 | 2020-03-03 | Translate Bio, Inc. | Liver specific delivery of messenger RNA |
| US11174500B2 (en) | 2018-08-24 | 2021-11-16 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11173190B2 (en) | 2017-05-16 | 2021-11-16 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of codon-optimized mRNA encoding CFTR |
| US11224642B2 (en) | 2013-10-22 | 2022-01-18 | Translate Bio, Inc. | MRNA therapy for argininosuccinate synthetase deficiency |
| US11254936B2 (en) | 2012-06-08 | 2022-02-22 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| US11253605B2 (en) | 2017-02-27 | 2022-02-22 | Translate Bio, Inc. | Codon-optimized CFTR MRNA |
| US12195505B2 (en) | 2018-11-21 | 2025-01-14 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
-
1963
- 1963-11-27 GB GB4679863A patent/GB1072118A/en not_active Expired
- 1963-11-29 BE BE640639A patent/BE640639A/xx unknown
- 1963-11-29 AT AT956163A patent/AT258875B/en active
Cited By (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664848A (en) | 1982-12-23 | 1987-05-12 | The Procter & Gamble Company | Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties |
| US9006487B2 (en) | 2005-06-15 | 2015-04-14 | Massachusetts Institute Of Technology | Amine-containing lipids and uses thereof |
| US8969353B2 (en) | 2008-11-07 | 2015-03-03 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US11414393B2 (en) | 2008-11-07 | 2022-08-16 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US10844028B2 (en) | 2008-11-07 | 2020-11-24 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US10189802B2 (en) | 2008-11-07 | 2019-01-29 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US9556110B2 (en) | 2008-11-07 | 2017-01-31 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US10576166B2 (en) | 2009-12-01 | 2020-03-03 | Translate Bio, Inc. | Liver specific delivery of messenger RNA |
| US9193827B2 (en) | 2010-08-26 | 2015-11-24 | Massachusetts Institute Of Technology | Poly(beta-amino alcohols), their preparation, and uses thereof |
| US10117934B2 (en) | 2011-03-28 | 2018-11-06 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US10933139B2 (en) | 2011-03-28 | 2021-03-02 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US11338044B2 (en) | 2011-06-08 | 2022-05-24 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
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| US9597413B2 (en) | 2011-06-08 | 2017-03-21 | Shire Human Genetic Therapies, Inc. | Pulmonary delivery of mRNA |
| US10413618B2 (en) | 2011-06-08 | 2019-09-17 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US11291734B2 (en) | 2011-06-08 | 2022-04-05 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US10350303B1 (en) | 2011-06-08 | 2019-07-16 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US11185595B2 (en) | 2011-06-08 | 2021-11-30 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US10507249B2 (en) | 2011-06-08 | 2019-12-17 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US11052159B2 (en) | 2011-06-08 | 2021-07-06 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US9308281B2 (en) | 2011-06-08 | 2016-04-12 | Shire Human Genetic Therapies, Inc. | MRNA therapy for Fabry disease |
| US10888626B2 (en) | 2011-06-08 | 2021-01-12 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US11254936B2 (en) | 2012-06-08 | 2022-02-22 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| US9227917B2 (en) | 2012-08-13 | 2016-01-05 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US9439968B2 (en) | 2012-08-13 | 2016-09-13 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US11510937B2 (en) | 2013-03-14 | 2022-11-29 | Translate Bio, Inc. | CFTR MRNA compositions and related methods and uses |
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Also Published As
| Publication number | Publication date |
|---|---|
| AT258875B (en) | 1967-12-11 |
| BE640639A (en) | 1964-05-29 |
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